


Spring Cleaning

by YlvaUllsdotter



Series: Experimental [1]
Category: Supernatural
Genre: 18+, Anal Play, Anal Plug, BDSM, Bondage, D/s dynamic, Dean Winchester - Freeform, Dean x Reader, F/M, Fanfiction, Handcuffs, Maybe - Freeform, NSFW, One-Shot, Reader Insert, SPN - Freeform, Smut, Strap-On, Supernatural - Freeform, Top!Reader, Vibrator, asexual!Reader, bottom!Dean, dildo
Language: English
Status: Completed
Published: 2018-05-08
Updated: 2018-05-08
Packaged: 2019-05-04 02:06:13
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,980
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14582556
Author URL: https://archiveofourown.org/users/YlvaUllsdotter/pseuds/YlvaUllsdotter
Summary: While you're cleaning the Bunker, Dean accidentally comes across your box of toys. He's surprised and curious. You're game.





	Spring Cleaning

**Author's Note:**

> I came up with the idea for this fic for [@thing-you-do-with-that-thing](http://thing-you-do-with-that-thing.tumblr.com/)’s Seasons of Love - Bloom of Spring challenge, but then when I saw the prompt for [@andtheraincamefalling](http://andtheraincamefalling.tumblr.com/%22)’s Spring Fling Challenge, I thought it could so easily be worked into this one, so I am doing what I’ve never done before and combining two challenges in one fic. The prompt for the SoL challenge was Spring Cleaning. The prompt for the Spring Fling challenge was “This is awkward.”  
> Mind the tags.  
> I apologize for nothing.

“Let’s do this!” You shoved a mop and bucket at Dean, whose expression said very clearly that he was not at all pleased with the way things had worked out. Ignoring the pouting Winchester, you gave him a bright smile and pointed down the hall in the general direction of the kitchen. “You mop the kitchen while I dust and vacuum the library and war room, then we’ll do the bedrooms.” You voice left no room for objections, so Dean headed, grumbling, to the kitchen while you went on to the larger spaces.

While you went over each bookshelf with a just barely damp microfiber cloth, you could hear Dean’s displeasure as he mopped the kitchen, and it made you grin to yourself. Once you had the vacuum cleaner going, it drowned out all sound and you were actually startled to find Dean mopping the floor in the war room as you finished up in the library. When he caught you staring at him in shock, he shrugged.

“I was done in the kitchen,” he muttered while keeping his eyes on the floor.

Huffing a quiet laugh at his demeanor, you pushed the cleaning supplies into a corner in the hallway, leaving them accessible for later, then went to dust and clean out the guest rooms and your own room, leaving Dean with his and Sam’s rooms.

The guest rooms were quickly done, only being furnished with the bare minimum. The beds did not even have linens on them, to save on laundry. You turned the mattresses and dusted all the surfaces, then headed to your own room.

As you walked down the hallway, you could hear Dean rummaging in Sam’s room, which was down the hall. Your room was in between the boys’ rooms, and closest to the showers. You set down the box you were carrying outside your door, leaving it there to put in storage later. It was just some spare items you had collected in the guest rooms that you felt were better off in storage. To the sounds of Dean rummaging in his brother’s room, you entered your own.

After the almost bare guest rooms, you almost felt at a loss when you looked at your own room, filled with the clutter of your life. Weapons, mementos, photos, lore books, all spread out across every surface. With a sigh, you decided to just start with the desk right by the door and work your way around the room.

Once you got going, you quickly lost track of time as you sorted items all while dusting them and the surfaces they were on. As you were turning your mattress, you noticed the box under your bed, sitting there all but forgotten. You pulled it out and opened it, a wistful smile crossing your face as you plucked items out of the box, remembering times you had used them. With a shake of your head, you hefted the box and set it on the newly cleared desk, deciding to take it to storage as well, since you could not see that you would get to use those things any time soon.

Satisfied with your work, you decided to take a little break for food. You could still hear Dean in Sam’s room and decided to make something for the both of you.

* * *

Dean was pouting, and he knew it. He figured he had a right though, having been conned into stupid spring cleaning by Y/N. He should have known better than to fall for her chipper little act. He dropped the pile of books on Sam’s desk with a loud thud, biting back a growl. When he looked back over the room, he shrugged to himself. It would have to do. He had no desire to spend any more time rummaging through his brother’s stuff anyway. Leaving the door open, he shuffled down the hall towards his own room. As he passed Y/N’s room, he glanced through the door. Two steps past her door, he stopped, as what he had seen registered in his mind. He backtracked and peeked his head around the doorframe, and looking straight into the box on her desk. His eyes went wide with surprise. The box was full of sex toys! And not just vibrators and dildos either. There were several types of cuffs, both leather and metal, and some sort of contraption of leather straps. Some of the things he could not even begin to guess what they were for, and some he had only seen in pornos before. He reached out to pick one of the items up, and just as his fingers touched the smooth silicone, Y/N’s voice called out his name from down the hall. Dean pulled his hand back as if he had been burned, his cheeks warm as he blushed. Hoping she would think he was just warm from working, he headed to the kitchen to see what she wanted, the images of what he had seen swirling in his head, mixing with images his mind conjured up of her using those things.

* * *

You noticed the flush in Dean’s cheeks as soon as he entered the kitchen and you might have brushed it off as the healthy glow of exertion, if not for the fact that the tips of his ears were also red, which was a sure sign of embarrassment. Filing that away, you offered Dean a beer and handed him a plate with your signature sandwich. The two of you ate in silence at the table in the kitchen, Dean seeming to almost deliberately keep his mouth full and his eyes on his food, as if he was avoiding you. As soon as he finished, he mumbled thanks and took off down the hall to his own room.

Something was definitely up with him. As you cleaned up after the two of you, your mind mused on the puzzle, and you grinned to yourself at the thought that maybe he’d found his brother’s porn.

Dean’s door was closed as you made your way back to your own room, finding the door open. As you reached for the box on your desk, you suddenly had a thought. You let go of the box and stepped out of the room, moving so that you were turned as if you were walking from Sam’s room to Dean’s. Suddenly Dean’s behavior made much more sense, and your lips quirked up in a grin. Perhaps the box could stay a little longer.

Picking up the other box, from outside your door, you deposited it in one of the lesser used storage rooms, leaving it neatly on a shelf out of the way. On your way back, you stopped and knocked on Dean’s door. He opened it almost immediately, finding himself only a foot away from you.

“Hey, could you help me turn my mattress?” You managed to make the question sound completely innocent.

“Uhm, yeah, sure,” Dean glanced behind him before slipping through the door and closing it.

You walked next to him, letting your hand brush against his ‘accidentally’ in the few steps it took to get to your room. You saw him glance at the box and blush as he entered your room, and suppressed a grin. When he looked away from the box to your bed, he found it freshly made with clean linens and he looked up at you with a confused frown.

“Oh yeah, I forgot I did that earlier. My bad.” You shrugged at him with an apologetic smile. “But hey, since you’re here, maybe you can help me with this?” You went on, placing a hand nonchalantly on the edge of the open box.

Dean swallowed hard, and your smile widened into a grin as he tried to look anywhere but the box or your face.

“Err, yeah, uhh, sure. What do you want to do with it?” He stammered and cleared his throat.

“Actually, I’m not sure. I was going to put it in storage, but now I’m thinking maybe not. What do you think?” Your tone was teasing and it got Dean’s attention. “I mean, you’ve already seen it, haven’t you?” You called him out in the same teasing tone.

“Well, **this is awkward** ,” he cleared his throat again, his face red with embarrassment as his hand came up to rub the back of his neck.

You placed your hand on his arm, feeling him flinch at the touch, and made him look at you.

“It’s only awkward if you let it be,” you assured him with a smile. “It’s not something we’ve ever talked about, but now that the cat’s out of the bag, or box”, you winked at him, “we might as well acknowledge it, don’t you think?”

Dean nodded hesitantly, still uncertain where you were going with this.

“So you saw my box of toys. I’m sure you have questions, so go ahead, ask me anything.”

His green eyes flickered to yours, then glanced off the box, and went on to shift around the room, as if looking for something normal to offset the weird. You rolled your eyes at him.

“Dean Winchester, I never thought you would be such a prude. C’mon, I’m giving you a free pass here, ask me anything and I promise to answer honestly.” You failed to keep a slight edge of command out of your voice, and you saw Dean straighten almost unconsciously, his eyes seemingly forced to the items in the box. It made you feel a little bad, knowing about his childhood, but it was done and there was no taking it back now.

He cleared his throat again, shoving his hands into his pockets. “I don’t even know what to ask”, he confessed. “I mean, some of these things I’ve seen before, but a few of them I have no idea what they even are.”

“Ok, well, it’s a place to start. Let’s go item by item and you can ask whatever you want, ok?”

He nodded and you grabbed the first item your hand landed on, a medium sized purple vibrator of smooth plastic. You held it up and Dean’s eyes flicked to it, then away.

“You’re imagining me using this, aren’t you?” You teased him, his deepening blush confirming your guess. “I have, many times. It’s not my favorite, but it gets the job done. You want to try it?” You held it out to him and he blinked rapidly as if processing what you had just said. He shook his head and kept his hands in his pockets so you shrugged and set the item aside on the desk, reaching in to pick up a set of four fur-lined leather cuffs. You liked to store them snapped together, so none of them would get lost in the clutter.

“What about these?” You smiled as you held them up, vivid images of the last time you used them playing in your head.

Dean glanced at the cuffs and blushed again and you waited for him to speak. “Uhm, how do...I mean, are those for you, or…?” He trailed off uncertainly.

You nodded at his question. “That’s a fair question. I’ve tried them, but it’s just not my jam. I prefer to use them on someone else,” you explained while unsnapping the carabiners holding them together. “Wanna try?” You winked at Dean, half expecting him to run screaming from your room. Color you surprised when he nodded, almost imperceptibly.

Keeping your eyes on his, you undid one of the wrist cuffs and held it out. Dean placed his wrist in the cuff and stood perfectly still while you fastened it and rotated it on his wrist. It was partly to move the fastenings into the right position, and partly to make sure it was not too tight. Dean’s eyes were riveted to the cuff on his wrist, and your fingers moving it. When you let go, he flexed his wrist as if to test what it felt like, then held out his other hand. Hiding your shock, you fastened the other cuff on him, then moved, slowly, behind him. You pulled his arms behind his back and fastened the cuffs together. There was enough space between them that he could have easily reached the carabiner and released it, but he only pulled a little at the restraints, then let his arms relax.

“You ok?” You asked him, concerned.

He only nodded at first, swallowing again and clearing his throat. “Yeah. It’s not so bad. I mean, they’re more comfortable than rope,” he tried to joke, making you huff a laugh. You reached in and released the cuffs, then came around him, returning to your previous position. He held out each arm in turn as you unfastened the cuffs and set them down on the desk. As you did so, he surprised you again as he reached into the box and came out with one of your favorite items.

“What’s this for? It looks dangerous,” he held it up and examined it as if it was a foreign artifact.

You took it from him, your other hand grasping his wrist lightly and pulling his hand towards you. Watching his face, as he watched your movements, you rolled the Wartenberg wheel over the palm of his hand, causing him to visibly shiver.

“It’s called a Wartenberg wheel, or just pinwheel, and it’s one of my favorite toys. Feels pretty good, doesn’t it?” You explained, still watching him as he had to swallow hard again before he could speak.

“Yeah, I...uhh...that was ok. It didn’t hurt,” he stammered.

When he kept his hand still, you decided to give him another taste, slowly rolling the wheel over the meaty part of his palm, then over his wrist and along his forearm all the way to the rolled sleeve of his flannel. He let out a quiet gasp when you stopped, his eyes half closed, lips slightly parted. With a small smile, you let go of his wrist and set the wheel aside. Giving him time to compose himself, you turned your attention to the contents of the box, pulling out one of several anal plugs. The one you picked was quite simple, a beginner size with no frills, just a silicone plug with a wide base. By the time you looked back up at Dean, he had regained his composure and was looking at the item in your hand with dread.

“I’m pretty sure I know what that is,” he choked out, looking apprehensive.

“Oh good,” you chirped cheerfully. “Wanna try it?”

Your question had Dean sputtering incoherently, interrupted by your laugh.

“Oh, Dean, you should see your face right now! Priceless!” You howled with laughter, clutching your stomach.

“Not funny, Y/N. Not funny at all.” Dean was pouting again, and you found it adorable. He was however also blushing furiously, which you found curious.

Still chuckling, you rolled the plug in your hands, your eyes finding Dean’s as you cocked your head. “I dunno, I thought it was pretty funny. Also, I think you wanna.” Your tone was challenging and Dean’s blush deepened.

“I...I don’t...I mean…,” he stammered, his eyes suddenly shifty.

“Mmhmm, I think you do. You are curious, Dean Winchester,” you teased lightly, your hands caressing the silicone suggestively. “If you just admit you wanna, I can help you,” the challenge clear in your voice.

Dean threw his hands up in frustration, his eyes locking on yours. “Fine, I’m curious, ok. I just don’t know if I’m ready for...that,” he nodded towards the toy in your hands.

Setting it aside, you nodded. “That’s fine, we can work up to it. Now that we’ve established that you want to try, why don’t you tell me what it was that caught your attention in the first place?”

Looking down into the box, seemingly more at ease now, Dean’s eyes flicked from item to item, until he finally reached in and pulled out the bundle of leather straps.

“What’s this for?” He asked, more open now that his secret was out.

Taking the straps from his hand, you straightened them somewhat before slipping it on over your jeans, fastening each strap in place carefully. Dean still looked confused, so you reached into the box and pulled out the accompanying item, settling it in place. Dean’s expression was one of wary understanding.

Squinting at him, you smirked. “You’ve seen one of these before, haven’t you?”

He shrugged and nodded, blushing again. “I do watch porn, you know,” he tried to explain, but trailed off when you just smirked at him.

Stroking the purple silicone strap-on dildo slowly and suggestively, you kept your eyes on Dean’s, your tongue flicking out to wet your lips. The dildo was not one of your larger ones, at a guess you would say it was probably smaller than Dean’s actual cock, but it was just right for a beginner, and one of your favorites. A lot of people had the misconception that a strap-on dildo had to be huge to be valid, but the truth was that a smaller one worked much better, especially if you wanted to get all of it inside.

Stepping in close to Dean, you caressed his arms, your hands moving over his shoulders and down his back to cup his ass through his jeans. Pressing him closer to you, your silicone cock rubbed against Dean’s real one and his hands came up to grasp your arms as a strangled moan ripped from his throat. You rolled your hips, grinding your cocks together and got a ragged gasp as a reward before you pulled away.

When his green eyes found yours again, he was flushed from more than just embarrassment and you gave him a reassuring smile as you undid the straps, laying the contraption on the desk next to the other items. You noticed Dean’s eyes kept returning to your lips, and with a slight internal sigh, you took his hand, pulled out the desk chair, and made him sit down. You walked over to the edge of the bed and sat down as well.

“Dean, there’s something I need to tell you before we go any further,” you started, your tone serious.

Dean nodded, looking concerned. “Go on.”

“I know that to you, to most people, these things are highly sexual. I’m guessing that you are thinking about us, you and I, having sex,” you continue, watching Dean’s face for clues.

“Well, yeah. I mean, that’s what all this is for, isn’t it? They’re called ‘sex toys’, Y/N,” Dean pointed out, frowning in confusion.

You nodded. “Yes, that’s true, but here’s the thing. I don’t actually want to have sex with you.”

Dean looked like you had just told him the sky was purple and the moon was made of cotton candy. “Uhm...what?”

“I’m not explaining myself very well,” you sighed. “You enjoy sex, right?” Dean rolled his eyes. “Well, I don’t.” He looked even more confused. When he looked like he was about to weigh in, you held up a hand to stop him. “Don’t say I just haven’t met the right guy. Trust me, I’ve been with some pretty great guys, and ladies,” Dean’s eyebrows shot up, but you went on, “and it just doesn’t do it for me. A few years ago, I finally found out there’s a term for someone like me. I’m asexual.”

Dean cocked his head, still frowning, but clearly listening.

“I’m not one hundred percent asexual though, I still can get turned on, just not by actual sex. If we do this, I need you to understand that I will never sleep with you, Dean.” You looked him straight in the eyes, to make sure he understood what you were saying.

Dean was quiet for a long while, processing. Finally, he spoke up.

“So, like, never?” You shook your head. “Then...what...I don’t get it.”

“It’s ok, it’s usually difficult for sexual people to understand. When I touch you, you feel arousal, right?” Dean nodded. “Well, when you touch me, I don’t feel that. I mean, it doesn’t feel repulsive, I just don’t feel the arousal.”

“So, what do you get out of,” he waved his hands vaguely, “this?”

“Well...have you ever heard of a mental orgasm?” Dean shook his head. “When I’m with someone, tie them up, do things to them with my toys, make them feel good, it makes me feel good emotionally and mentally. It’s like an emotional release.” You looked at Dean, hoping you made sense.

He nodded slowly. “I’m not sure I get it entirely, but I guess it’s one of those things you gotta experience to understand.” He looked at you for confirmation and you nodded. “So, if you don’t wanna have sex with me, but you still wanna do the other things, help me experiment, I’m cool with that.” You failed to hold back your relieved smile and he returned it. “I mean, I’m usually all about making the lady feel good, but if doing those things to me makes you feel good, then I’ll be ok with that.”

“You don’t know how much it means to me that you understand, Dean,” you told him, the relief evident in your voice. “I’ve missed having someone to play with, but it’s hard to find someone who understands, you know.”

Dean nodded and returned your smile. “I guess I can understand that.” He fidgeted a bit in his seat. “So, uhm, how do we do this? I mean, I know what I wanna do, but since that’s not your thing, you gotta tell me what you want.”

“Oh don’t worry, you’ll know,” you smirked and winked at him, “just do what I tell you and you’ll be good.”

Dean nodded, still looking a bit uncertain. You stood up and went over to him, taking his hand and pulling him to his feet. You were taller than average, but Dean was still a good half head taller than you, so you had to tilt your head back to look up at him.

“Why don’t we start right now? We have the Bunker to ourselves for at least another thirty-six hours,” you smiled suggestively at Dean.

“Uh, ok...what-,” Dean’s words cut off when you placed two fingers over his plump lips.

“Take your clothes off,” you told him, your voice calmly assertive now that you were in your element.

Without another word, as soon as you stepped back, Dean peeled off his flannel. His t-shirt, jeans, and socks quickly followed, all of it piled on the chair he had vacated. He hesitated at his boxers and you nodded at him, motioning with your hand for him to go on. When he was completely naked, you took his wrist and pulled him to stand in the middle of the floor, letting you admire his body. When you licked your lips and brushed your fingertips over the flushed skin of his chest he raised an eyebrow at you.

“Shush. Just ‘cause I don’t get sexually aroused doesn’t mean I can’t admire an aesthetically pleasing body,” you explained before he had time to comment. He smirked at the thinly veiled praise and preened.

“You gotta tell me what you want, Dean. I know you’re sexually experienced, so what is it you’re curious about? What do you want me to do to you?”

Dean blushed again, in spite of being buck naked in front of you, he still was embarrassed talking about his desires. When he failed to get any words out, your hand caressed his back soothingly, up and down his spine, fingers brushing against the top of his ass cheeks on each downward stroke.

“If we can’t talk about it, we shouldn’t be doing it,” you smiled, “isn’t that what Jody always says? So, tell me, Dean. What do you want?”

Clearing his throat, Dean stuttered, then swallowed, cleared his throat again.

“Uhm, I want to try those things,” he nodded towards the desk. “The, uhm, plug,” he had to stop and clear his throat again, “and uhh other things.”

“Good boy, Dean. You gotta use your words. Communication is key in this sort of experimentation. I can read your body language, but I’m not a mind reader.” You patted his ass when he nodded. “So you’re curious about anal play.” He nodded again. “Have you ever tried anything on your own, or with someone?”

“Once, or twice.” He blushed furiously now and you kept up the soothing caresses up and down his back.

“I’ll need details, Dean. So I know where to start,” you prodded.

“Uhm, just the girl...err lady...sticking a finger...y’know...back there,” he stammered, barely able to get the words out.

You moved your hand down and let your other hand join in, caressing his ass cheeks, squeezing them, kneading the flesh.

“Good boy. I know that was hard for you, but it’s good to talk about it. So since you’re curious now, I’m assuming you liked what those women did?” You prodded further and he nodded in response, leaning into your touch. “And now you’re curious to try more?” You kept prodding, as your hands teased his ass, spreading his cheeks apart, your fingers brushing along his crack, making him shiver with the sensation.

“Yes…,” the word came out on a slight hiss as one of your fingers brushed feather-light over his puckered muscle, making you smile at how reactive he was.

Resting your hands on his hips, you prodded him to move forward until he was right at the foot of your bed. With your hands you helped him into position, bent over, his hands resting on the mattress, legs spread almost as wide as the bed. From his body language, you knew he was still tense, probably a little apprehensive as well. This was all new to him, and you needed to go slowly.

Standing behind him, you slipped one hand around to wrap your fingers around his cock, which was half hard by now. The other hand caressed his ass, down along his crack, to find his prostate. He grunted when you found it, the feeling making him arch his back and thrust into your hand.

“Feels good, doesn’t it?” You teased, rubbing circles over the spot, softly, so as not to overwhelm him. His only response was another grunt and you moved your fingers away. “Use your words, Dean,” you admonished.

“Uhmmm yes, it feels good, Y/N. Please do it again.”

Smiling to yourself, you let your fingers return to the spot and resumed the gentle massage, all the while slowly stroking his cock.

“Do you want me to tell you what I’m going to do before I do it, Dean? Or would you rather I just surprise you?”

“I...uhh...I don’t…,” he stammered, clearly unable to think straight.

You moved your hands away from him, coming around to sit on the edge of the bed and lifting his head so you could look into his eyes.

“Warn you first, or surprise you?” You repeated your question, watching him blink to process.

“Su-surprise me,” he breathed. You nodded and let go of his chin, moving back behind him. You grabbed the bottle of lube from the box, popped the cap and squirted some into your palm, setting the bottle on the floor by the bed within easy reach. You spread the lube on both hands before resuming stroking his cock, to his grateful moan. Moving your other hand to his ass, you traced a finger from just behind his balls, up along his crack until you found his puckered hole. Keeping him distracted with slow strokes to his slick cock, you liberally coated his anus with lube, circling the muscle with two fingers, gently massaging it.

When he started thrusting his hips, you slowly worked a single finger in past the muscle, to his increased moans and groans of pleasure. You let him fuck himself on your finger as he thrust his cock into your hand, slowly inserting it deeper until you found the spot. Crooking your finger, you made sure your fingertip would press against it on each thrust, drawing choked ragged moans from Dean.

“I can’t...I’m gonna…,” he panted.

You knew he did not yet have the discipline to hold back, so you sped up your strokes, coaxing his orgasm from him. He collapsed to his knees, his hips thrusting, rutting his cock against your hand and the bed as he came with a whimpered groan.

“I’m sorry, I’m so sorry, I’m-,” he panted before you cut him off.

“Shh, it’s ok. It was your first time, don’t worry about it.” You reassured him, wiping the lube from your hands before soothingly caressing his back and ass. “Next time, you’ll last longer,” you added, certain he could hear the smile in your voice.

When he had recovered, he raised himself from the bed, looking down at the mess he had made and blushing.

“I messed up your clean sheets,” he said, embarrassed.

“It’s ok, you can change them for me. How do you feel?”

Dean was quiet for a while, you could see he was processing, trying to find the words to answer your question.

“I’m...I feel ok. Better than ok. Really good actually,” he grinned at the realization and you had to grin back at him. “I’m really looking forward to next time,” he added, with a wink.

You had to laugh. “I’m glad you enjoyed it. I think you’ll enjoy the rest of what I have planned to. But for now, let’s get you cleaned up and finish our spring cleaning.”

Dean’s face fell and he groaned.

“I forgot that’s what we were doing,” he grumbled, “I hate cleaning!”


End file.
